One entry, multiple calendars

I know it's not a completely new question but I didn't see any resolution about this, here is my issue.

I have a shared calendar with my office where everyone in the office can see who in the office is on PTO.
I have a shared calendar with my team (spreaded over offices) where everyone in the team can see who in the team in on PTO
I have my personal calendar that display "free/busy" status when someone from the company wants to schedule a meeting with me.

At the moment I have to enter 3 times my PTO for each of those calendars. Seems to me that I would benefit from a feature where I can select multiple calendars for my entry.

Also to reduce the pain, I thought I could tell at least one of the 2 shared calendars to report that as free/busy so I don't have to enter anything in my personal calendar but then when anyone says he's on PTO I'm marked as being away...

I'm a pretty new user but I'll share what I know. I haven't found a way to post on multiple calendars. But the issue that you are having with showing yourself as out - I think is because you probably created that calendar under your own user name. For this we have a department calendar that is shared out where we put vacation information. You can give yourself management rights and then give everyone else view only rights. The calendar was created under the department's log in, so you can enter on it and it won't show you as busy. Make sure when you are sharing it out though to mark the box that says Exclude from free/busy time. Hope this helps. K

I don't know if this will match your requirements exactly, but this is the story of 'Staff Whereabouts':

Once upon a time someone (HR) decided that they would like to have a single calendar where they could see what people were doing and where they would be, all in one place. They created a calendar, called 'Staff Whereabouts', that they shared with everybody and everybody could post their appointments on for when they were not going to be in their usual location.

This had two major drawbacks:
1) Everyone had to post things like business trips, holidays etc. in both calendars
2) Those of us with mobile devices, who subscribed to the shared calendar would be cheerily informed at 11:55 each night about the people who were going to be out-and-about all day tomorrow!

Then one day, after being woken up at 2:55 am to be told that someone in another timezone had a meeting, I came up with the following which we have used ever since.

1) Create a resource called 'Staff Whereabouts' <whereabouts@mydomain.com>
2) Set its scheduling policy to: 'Auto accept always'
3) Share its calendar read-only with everyone
4) Publish the calendar via an iframe on a page on the Intranet - other methods are available.

Now, to add our whereabouts to the public calendar we just 'invite' 'Staff Whereabouts' to the appointment, it auto-accepts and the appointment shows on the globally-available calendar.